CA2830027C - Novel bicyclic pyridinones - Google Patents
Novel bicyclic pyridinones Download PDFInfo
- Publication number
- CA2830027C CA2830027C CA2830027A CA2830027A CA2830027C CA 2830027 C CA2830027 C CA 2830027C CA 2830027 A CA2830027 A CA 2830027A CA 2830027 A CA2830027 A CA 2830027A CA 2830027 C CA2830027 C CA 2830027C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- dihydro
- fluoro
- imidazol
- dione
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 bicyclic pyridinones Chemical class 0.000 title claims description 186
- 150000001875 compounds Chemical class 0.000 claims abstract description 215
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 97
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 77
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000001153 fluoro group Chemical group F* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 15
- 208000024827 Alzheimer disease Diseases 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 8
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 8
- 208000012902 Nervous system disease Diseases 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 208000020016 psychiatric disease Diseases 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 208000025966 Neurological disease Diseases 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical group C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- USQJUMKNJWUXHW-UHFFFAOYSA-N [1]benzofuro[3,2-c]pyridine Chemical group C1=NC=C2C3=CC=CC=C3OC2=C1 USQJUMKNJWUXHW-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical group N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- ZGSNZVRXASCXRP-UHFFFAOYSA-N 5-methoxy-1h-pyrazole Chemical group COC=1C=CNN=1 ZGSNZVRXASCXRP-UHFFFAOYSA-N 0.000 claims description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- 230000000926 neurological effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical group C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims 4
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- IVDMVAFKQDDZGH-AWEZNQCLSA-N 2-[(2s)-1-[4-chloro-2-(trifluoromethyl)phenoxy]propan-2-yl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C([C@H](C)N1C(C=2N(C(C(N3C=C(C)N=C3)=CC=2)=O)CC1)=O)OC1=CC=C(Cl)C=C1C(F)(F)F IVDMVAFKQDDZGH-AWEZNQCLSA-N 0.000 claims 1
- WNKIZPPVGKAWKE-UHFFFAOYSA-N 2-[2-[(2,2-difluoro-1,3-benzodioxol-4-yl)oxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C=3OC(F)(F)OC=3C=CC=1)C2=O WNKIZPPVGKAWKE-UHFFFAOYSA-N 0.000 claims 1
- LEHPUPBPVUBARN-UHFFFAOYSA-N 2-[2-[(2,2-difluoro-1,3-dihydroinden-4-yl)oxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C=3CC(F)(F)CC=3C=CC=1)C2=O LEHPUPBPVUBARN-UHFFFAOYSA-N 0.000 claims 1
- DQQPPDXEPYOQEC-UHFFFAOYSA-N 2-[2-[2-(3-bicyclo[1.1.1]pentanyl)-4-chlorophenoxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC(Cl)=CC=1)C13CC(C1)C3)C2=O DQQPPDXEPYOQEC-UHFFFAOYSA-N 0.000 claims 1
- WOARPCISPWAXFG-UHFFFAOYSA-N 2-[2-[2-(3-bicyclo[1.1.1]pentanyl)phenoxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC=CC=1)C13CC(C1)C3)C2=O WOARPCISPWAXFG-UHFFFAOYSA-N 0.000 claims 1
- YQSXKNVPEQLXJQ-UHFFFAOYSA-N 2-[2-[[4-fluoro-2-(trifluoromethyl)-1,3-benzothiazol-7-yl]oxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C=3SC(=NC=3C(F)=CC=1)C(F)(F)F)C2=O YQSXKNVPEQLXJQ-UHFFFAOYSA-N 0.000 claims 1
- AHERSACVYXVWEK-UHFFFAOYSA-N 7-(4-methylimidazol-1-yl)-2-[2-[2-[2-(trifluoromethyl)-1,3-thiazol-4-yl]phenoxy]ethyl]-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC=CC=1)C=1N=C(SC=1)C(F)(F)F)C2=O AHERSACVYXVWEK-UHFFFAOYSA-N 0.000 claims 1
- XNBWJMQONCSXNL-UHFFFAOYSA-N 7-(4-methylimidazol-1-yl)-2-[2-[2-[3-(trifluoromethyl)-1,2,4-thiadiazol-5-yl]phenoxy]ethyl]-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC=CC=1)C=1SN=C(N=1)C(F)(F)F)C2=O XNBWJMQONCSXNL-UHFFFAOYSA-N 0.000 claims 1
- WANTWYYPVUJSRC-UHFFFAOYSA-N 7-(4-methylimidazol-1-yl)-2-[2-[2-[3-(trifluoromethyl)-1,2-oxazol-5-yl]phenoxy]ethyl]-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC=CC=1)C=1ON=C(C=1)C(F)(F)F)C2=O WANTWYYPVUJSRC-UHFFFAOYSA-N 0.000 claims 1
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- 229940099433 NMDA receptor antagonist Drugs 0.000 claims 1
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- 229940127236 atypical antipsychotics Drugs 0.000 claims 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 144
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 81
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- 125000001424 substituent group Chemical group 0.000 description 70
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 65
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 39
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- 150000001721 carbon Chemical group 0.000 description 19
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 18
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- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 16
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- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/695—Silicon compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
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| US201161470076P | 2011-03-31 | 2011-03-31 | |
| US61/470,076 | 2011-03-31 | ||
| US201261599022P | 2012-02-15 | 2012-02-15 | |
| US61/599,022 | 2012-02-15 | ||
| PCT/IB2012/051348 WO2012131539A1 (en) | 2011-03-31 | 2012-03-21 | Novel bicyclic pyridinones |
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| CA2830027A1 CA2830027A1 (en) | 2012-10-04 |
| CA2830027C true CA2830027C (en) | 2016-04-26 |
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|---|---|---|---|
| CA2830027A Expired - Fee Related CA2830027C (en) | 2011-03-31 | 2012-03-21 | Novel bicyclic pyridinones |
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| EP (1) | EP2691393B1 (cg-RX-API-DMAC7.html) |
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| AR (1) | AR085748A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2830027C (cg-RX-API-DMAC7.html) |
| ES (1) | ES2602794T3 (cg-RX-API-DMAC7.html) |
| TW (1) | TW201300384A (cg-RX-API-DMAC7.html) |
| UY (1) | UY33978A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2012131539A1 (cg-RX-API-DMAC7.html) |
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| MX2011008335A (es) | 2009-02-06 | 2011-09-06 | Ortho Mcneil Janssen Pharm | Novedosos compuestos heterociclicos biciclicos sustituidos como moduladores de la gamma secretasa. |
| TWI461425B (zh) | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| KR20120024555A (ko) | 2009-05-07 | 2012-03-14 | 얀센 파마슈티칼즈, 인코포레이티드 | 감마 세크레타제 조절제로서의 신규 치환된 인다졸 및 아자-인다졸 유도체 |
| AU2010272578B2 (en) | 2009-07-15 | 2015-03-05 | Cellzome Limited | Substituted triazole and imidazole derivatives as gamma secretase modulators |
| AU2011206635B2 (en) | 2010-01-15 | 2015-01-22 | Cellzome Limited | Novel substituted triazole derivatives as gamma secretase modulators |
| MX2013010970A (es) | 2011-03-24 | 2013-10-17 | Cellzome Ltd | Novedosos derivados de triazolil piperazina y triazolil piperidina sustituidos como moduladores de gamma-secretasa. |
| ES2555167T3 (es) | 2011-07-15 | 2015-12-29 | Janssen Pharmaceuticals, Inc. | Nuevos derivados de indol sustituidos como moduladores de gamma secretasa |
| MX2014009373A (es) | 2012-02-03 | 2014-08-27 | Teva Pharma | Uso de laquinimod para tratar pacientes con enfermedad de crohn que fallaron en la terapia de anti-tnfa de primera linea. |
| JP6106745B2 (ja) * | 2012-05-16 | 2017-04-05 | ヤンセン ファーマシューティカルズ，インコーポレーテッド | （特に）アルツハイマー病の治療に有用な置換３，４−ジヒドロ−２Ｈ−ピリド［１，２−ａ］ピラジン−１，６−ジオン誘導体 |
| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| US20140107154A1 (en) * | 2012-10-12 | 2014-04-17 | Teva Pharmaceutical Industries, Ltd. | Laquinimod for reducing thalamic damage in multiple sclerosis |
| JP2014101316A (ja) * | 2012-11-20 | 2014-06-05 | Toyobo Co Ltd | ベンゾ［１，２−ｄ；４，５−ｄ’］ビスチアゾール化合物の製造方法 |
| CN104918938B (zh) * | 2012-12-20 | 2017-08-15 | 詹森药业有限公司 | 新颖的作为γ分泌酶调节剂的三环3，4‑二氢‑2H‑吡啶并[1，2‑a]吡嗪‑1，6‑二酮衍生物 |
| US10246454B2 (en) | 2013-01-17 | 2019-04-02 | Janssen Pharmaceutica Nv | Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators |
| JP6425717B2 (ja) * | 2013-10-04 | 2018-11-21 | ファイザー・インク | ガンマセクレターゼモジュレーターとしての新規二環式ピリジノン |
| US10562897B2 (en) | 2014-01-16 | 2020-02-18 | Janssen Pharmaceutica Nv | Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators |
| MD4807C1 (ro) * | 2014-01-16 | 2022-12-31 | Fmc Corporation | Derivaţi de pirimidiniloxi-benzen utilizaţi ca erbicide |
| CN103787839B (zh) * | 2014-01-21 | 2015-12-02 | 苏州昊帆生物科技有限公司 | 合成2,3,4,5,6-五氟苯酚的方法 |
| MX369074B (es) * | 2014-04-01 | 2019-10-28 | Pfizer | Cromeno y 1,1a,2,7b-tetrahidrociclopropa[c]cromeno piridopirazinadionas como moduladores de la gamma secretasa. |
| CN103965093A (zh) * | 2014-04-04 | 2014-08-06 | 华南理工大学 | 2-全氟烷基吲哚类化合物及其制备方法和应用 |
| WO2015168103A1 (en) | 2014-04-29 | 2015-11-05 | Teva Pharmaceutical Industries Ltd. | Laquinimod for the treatment of relapsing-remitting multiple sclerosis (rrms) patients with a high disability status |
| MX368391B (es) | 2015-02-03 | 2019-09-30 | Pfizer | Ciclopropabenzofuranil-piridopirazindionas novedosas. |
| WO2016201168A1 (en) | 2015-06-10 | 2016-12-15 | Forum Pharmceuticals Inc. | Oxadiazine compounds and methods of use thereof |
| US11492325B2 (en) * | 2016-05-31 | 2022-11-08 | Human Biomolecular Research Institute | Compounds as inhibitors of sodium channels |
| WO2018031680A1 (en) * | 2016-08-10 | 2018-02-15 | Fronthera U.S. Pharmaceuticals Llc | Novel compounds, uses and methods for their preparation |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CN110256369A (zh) * | 2019-07-01 | 2019-09-20 | 中国人民大学 | 一种制备多氟烷基取代的异恶唑化合物的方法 |
Family Cites Families (114)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1419789A (en) | 1972-08-02 | 1975-12-31 | Pfizer | 2-trifluoromethyl-4-quinolinols |
| NO179904C (no) | 1992-09-04 | 1997-01-08 | Takeda Chemical Industries Ltd | Kondenserte heterocykliske forbindelser og deres anvendelse |
| US5750349A (en) | 1993-01-25 | 1998-05-12 | Takeda Chemical Industries Ltd. | Antibodies to β-amyloids or their derivatives and use thereof |
| NO309272B1 (no) | 1995-03-24 | 2001-01-08 | Takeda Chemical Industries Ltd | Cykliske forbindelser, preparater inneholdende forbindelsene samt mellomprodukter for fremstilling av forbindelsene |
| DE19709877A1 (de) | 1997-03-11 | 1998-09-17 | Bayer Ag | 1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate |
| NZ337765A (en) | 1997-04-09 | 2001-09-28 | Mindset Biopharmaceuticals Usa | Recombinant antibodies having specificity for beta-amyloid N-terminus and C-terminus and use in treating Alzheimer's Disease |
| US8173127B2 (en) | 1997-04-09 | 2012-05-08 | Intellect Neurosciences, Inc. | Specific antibodies to amyloid beta peptide, pharmaceutical compositions and methods of use thereof |
| GB9722520D0 (en) | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| TWI239847B (en) | 1997-12-02 | 2005-09-21 | Elan Pharm Inc | N-terminal fragment of Abeta peptide and an adjuvant for preventing and treating amyloidogenic disease |
| US6905686B1 (en) | 1997-12-02 | 2005-06-14 | Neuralab Limited | Active immunization for treatment of alzheimer's disease |
| CN1229296C (zh) | 1998-03-03 | 2005-11-30 | Ppg工业俄亥俄公司 | 浸渍玻璃纤维束以及包括它的产品 |
| US20020132817A1 (en) | 1998-03-19 | 2002-09-19 | Hideaki Natsugari | Heterocyclic compounds, their production and use |
| EP1145714A4 (en) | 1998-11-27 | 2004-12-15 | Takeda Chemical Industries Ltd | DRUGS |
| MXPA02008145A (es) | 2000-02-24 | 2004-04-05 | Univ Washington | Anticuerpos humanizados que secuestran al peptido beta amiloide. |
| DE10045112A1 (de) | 2000-09-11 | 2002-03-21 | Merck Patent Gmbh | Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems |
| AU2002239764B2 (en) | 2000-11-03 | 2007-06-21 | Proteotech, Inc. | Methods of isolating amyloid-inhibiting compounds and use of compounds isolated from uncaria tomentosa and related plants |
| EP1432444A4 (en) | 2001-08-17 | 2005-11-02 | Lilly Co Eli | ANTI-BETA ANTIBODIES |
| US20030195205A1 (en) | 2001-11-02 | 2003-10-16 | Pfizer Inc. | PDE9 inhibitors for treating cardiovascular disorders |
| DE10238723A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl-substituierte Pyrazolyprimidine |
| DE10238724A1 (de) | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
| EP1549315A4 (en) * | 2002-09-11 | 2007-05-23 | Merck & Co Inc | DIHYDROXYPYRIDOPYRAZINE-1,6-DION COMPOUNDS AS HIV INTEGRASE INHIBITORS |
| PL377769A1 (pl) | 2002-10-09 | 2006-02-20 | Rinat Neuroscience Corp. | Sposób leczenia choroby Alzheimera z zastosowaniem przeciwciał skierowanych przeciw peptydowi beta amyloidu i ich kompozycje |
| AU2003301439A1 (en) | 2002-10-16 | 2004-05-04 | Gilead Sciences, Inc. | Pre-organized tricyclic integrase inhibitor compounds |
| US20040220186A1 (en) | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
| WO2004110996A1 (en) | 2003-06-19 | 2004-12-23 | Pfizer Products Inc. | Nk1 antagonist |
| CA2538220A1 (en) | 2003-09-09 | 2005-03-24 | Takeda Pharmaceutical Company Limited | Use of antibody |
| US7572799B2 (en) | 2003-11-24 | 2009-08-11 | Pfizer Inc | Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors |
| GB0327319D0 (en) | 2003-11-24 | 2003-12-24 | Pfizer Ltd | Novel pharmaceuticals |
| CN1913778A (zh) | 2004-01-28 | 2007-02-14 | 默克公司 | 趋化因子受体活性的氨基环戊基吡啶并吡嗪酮调节剂 |
| EP1720847A1 (en) | 2004-02-02 | 2006-11-15 | Pfizer Products Incorporated | Histamine-3 receptor modulators |
| JP2007528394A (ja) | 2004-03-09 | 2007-10-11 | メルク エンド カムパニー インコーポレーテッド | Ｈｉｖインテグラーゼ阻害薬 |
| SI1742642T1 (sl) | 2004-04-14 | 2009-04-30 | Gilead Sciences Inc | Fosfonatni analogi inhibitorskih spojin HIV integraze |
| US7456164B2 (en) | 2004-05-07 | 2008-11-25 | Pfizer, Inc | 3- or 4-monosubtituted phenol and thiophenol derivatives useful as H3 ligands |
| EP1595881A1 (en) | 2004-05-12 | 2005-11-16 | Pfizer Limited | Tetrahydronaphthyridine derivates useful as histamine H3 receptor ligands |
| EP2298807A3 (en) | 2004-07-30 | 2011-05-18 | Rinat Neuroscience Corp. | Antibodies directed against amyloid-beta peptide and methods using same |
| FR2877015B1 (fr) | 2004-10-21 | 2007-10-26 | Commissariat Energie Atomique | Revetement nanostructure et procede de revetement. |
| GB0423356D0 (en) | 2004-10-21 | 2004-11-24 | Merck Sharp & Dohme | Therapeutic agents |
| WO2006069081A2 (en) | 2004-12-22 | 2006-06-29 | Washington University In St. Louis | USE OF ANTI-Aβ ANTIBODY TO TREAT TRAUMATIC BRAIN INJURY |
| UY29504A1 (es) | 2005-04-29 | 2006-10-31 | Rinat Neuroscience Corp | Anticuerpos dirigidos contra el péptido amiloide beta y métodos que utilizan los mismos. |
| WO2006121831A2 (en) | 2005-05-10 | 2006-11-16 | Merck & Co., Inc. | Hiv integrase inhibitors |
| AU2006245416B2 (en) | 2005-05-12 | 2012-02-23 | Pfizer Inc. | Anhydrous crystalline forms of N-[1-(2-ethoxyethyl)-5-(N-ethyl-N-methylamino)-7-(4-methylpyridin-2-yl-amino)-1H-pyrazolo[4,3-d]pyrimidine-3-carbonyl]methanesulfonamide |
| CA2603830A1 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Co Llc | PYRIDINE [2,3-B] PYRAZINONES |
| WO2006126082A2 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Company Llc | Pyridine [3,4-b] pyrazinones as pde-5 inhibitors |
| WO2006126083A1 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Company Llc | Pyridine [3 , 4-b] pyrazinone compounds as pde-5 inhibitors |
| CA2607499C (en) | 2005-06-22 | 2010-11-30 | Pfizer Products Inc. | Histamine-3 receptor antagonists |
| TW200713011A (en) | 2005-09-30 | 2007-04-01 | Hon Hai Prec Ind Co Ltd | System, method and electrical apparatus for data transferring |
| US8158673B2 (en) | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
| US20070197532A1 (en) | 2005-11-18 | 2007-08-23 | Cao Sheldon X | Glucokinase activators |
| JP5221144B2 (ja) | 2005-11-24 | 2013-06-26 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | モルホリンタイプ・シンナミド化合物 |
| US20070117839A1 (en) | 2005-11-24 | 2007-05-24 | Eisai R&D Management Co., Ltd. | Two cyclic cinnamide compound |
| WO2007063385A2 (en) | 2005-12-01 | 2007-06-07 | Pfizer Products Inc. | Spirocyclic amine histamine-3 receptor antagonists |
| WO2007069053A1 (en) | 2005-12-14 | 2007-06-21 | Pfizer Products Inc. | Benzimidazole antagonists of the h-3 receptor |
| PE20071321A1 (es) * | 2006-01-20 | 2007-12-29 | Schering Corp | Bencensulfonil-cromano, tiocromano, tetrahidronaftaleno e inhibidores de gamma secretasa relacionados |
| WO2007088450A2 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Chromane antagonist of the h-3 receptor |
| WO2007088462A1 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Spirochromane antagonists of the h-3 receptor |
| WO2007099423A1 (en) | 2006-03-02 | 2007-09-07 | Pfizer Products Inc. | 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists |
| TWI378091B (en) | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| EP2007749A2 (en) | 2006-03-13 | 2008-12-31 | Pfizer Products Inc. | Tetralines antagonists of the h-3 receptor |
| WO2007122466A1 (en) | 2006-04-21 | 2007-11-01 | Pfizer Products Inc. | Pyridine[3,4-b]pyrazinones |
| US8008287B2 (en) | 2006-05-16 | 2011-08-30 | Gilead Sciences, Inc. | Integrase inhibitors |
| EP2019093A4 (en) | 2006-05-19 | 2011-02-23 | Eisai R&D Man Co Ltd | CINEMA ACID AMID DERIVATIVE FROM THE UREA TYPE |
| WO2007138431A2 (en) | 2006-05-30 | 2007-12-06 | Pfizer Products Inc. | Azabicyclic ether histamine-3 antagonists |
| AU2008208653B2 (en) | 2007-01-22 | 2012-11-22 | Pfizer Products Inc. | Tosylate salt of a therapeutic compound and pharmaceutical compositions thereof |
| CA2676920A1 (en) | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperidine derivatives |
| CA2676715A1 (en) | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperazine derivatives for treatment of ad and related conditions |
| US20080207900A1 (en) | 2007-02-28 | 2008-08-28 | Teiji Kimura | Two cyclic oxomorphorin derivatives |
| WO2008137102A2 (en) | 2007-05-04 | 2008-11-13 | Torreypines Therapeutics, Inc. | Methods of modulating amyloid beta and compounds useful therefor |
| US8357682B2 (en) | 2007-05-07 | 2013-01-22 | Zhaoning Zhu | Gamma secretase modulators |
| EP2155740B1 (en) | 2007-05-11 | 2011-01-26 | F. Hoffmann-La Roche AG | Hetarylanilines as modulators for amyloid beta |
| US8426403B2 (en) | 2007-06-01 | 2013-04-23 | Zhaoning Zhu | Gamma secretase modulators |
| WO2008153792A2 (en) | 2007-06-01 | 2008-12-18 | Schering Corporation | Gamma secretase modulators |
| WO2008156580A1 (en) | 2007-06-13 | 2008-12-24 | Merck & Co., Inc. | Triazole derivatives for treating alzheimer's disease and related conditions |
| WO2009005729A1 (en) | 2007-06-29 | 2009-01-08 | Schering Corporation | Gamma secretase modulators |
| US20110009392A1 (en) | 2007-08-06 | 2011-01-13 | Schering Corporation | Gamma secretase modulators |
| US7935815B2 (en) | 2007-08-31 | 2011-05-03 | Eisai R&D Management Co., Ltd. | Imidazoyl pyridine compounds and salts thereof |
| NZ583515A (en) | 2007-08-31 | 2011-05-27 | Eisai R&D Man Co Ltd | Imidazole-pyridine derivative featuring a 1,2,4-triazole ring fused to a 5-7 membered ring, for treating a disease caused by amyloid-beta such as Alzheimer's, dementia, Down's syndrome, and amyloidosis |
| EP2200990A1 (en) | 2007-09-06 | 2010-06-30 | Schering Corporation | Gamma secretase modulators |
| CN101878202A (zh) | 2007-09-28 | 2010-11-03 | 先灵公司 | γ-分泌酶调节剂 |
| GB0720444D0 (en) | 2007-10-18 | 2007-11-28 | Glaxo Group Ltd | Novel compounds |
| WO2009061699A1 (en) | 2007-11-05 | 2009-05-14 | Schering Corporation | Gamma secretase modulators |
| CA2707722A1 (en) | 2007-12-06 | 2009-06-11 | Schering Corporation | Gamma secretase modulators |
| US8426595B2 (en) | 2007-12-11 | 2013-04-23 | Xianhai Huang | Gamma secretase modulators |
| CA2708151A1 (en) | 2007-12-11 | 2009-06-18 | Schering Corporation | Gamma secretase modulators |
| CN101896461A (zh) | 2007-12-13 | 2010-11-24 | 安姆根有限公司 | γ分泌酶调节剂 |
| CN101910142B (zh) | 2008-01-11 | 2013-07-10 | 弗·哈夫曼-拉罗切有限公司 | β-淀粉状蛋白的调节剂 |
| WO2009103652A1 (en) | 2008-02-22 | 2009-08-27 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| US20110027264A1 (en) | 2008-02-29 | 2011-02-03 | Xianhai Huang | Gamma secretase modulators for the treatment of alzheimer's disease |
| US20100137320A1 (en) | 2008-02-29 | 2010-06-03 | Schering Corporation | Gamma secretase modulators |
| BRPI0912539A2 (pt) | 2008-05-05 | 2015-10-13 | Amgen Inc | composto, composição farmacêutica , método para tratar uma doença, e, uso do composto. |
| TW201006801A (en) | 2008-07-18 | 2010-02-16 | Lilly Co Eli | Imidazole carboxamides |
| WO2010019393A1 (en) | 2008-08-13 | 2010-02-18 | Merck Sharp & Dohme Corp. | Pyrimidine derivatives for treatment of alzheimer's disease |
| US20110251172A1 (en) | 2008-08-13 | 2011-10-13 | Rivkin Alexey A | Purine derivatives for treatment of alzheimer's disease |
| EP2324009A1 (en) | 2008-08-27 | 2011-05-25 | Eisai R&D Management Co., Ltd. | Process for preparing certain cinnamide compounds |
| CN102177151A (zh) | 2008-10-09 | 2011-09-07 | 弗·哈夫曼-拉罗切有限公司 | β-淀粉样蛋白的调节剂 |
| US20110263529A1 (en) | 2008-11-06 | 2011-10-27 | Ruo Xu | Gamma secretase modulators |
| EP2356115A1 (en) | 2008-11-06 | 2011-08-17 | Schering Corporation | Gamma secretase modulators |
| EP2367826A4 (en) | 2008-11-06 | 2012-07-04 | Astrazeneca Ab | MODULATORS OF THE PROTEIN -AMYLOID |
| CA2743196A1 (en) | 2008-11-10 | 2010-05-14 | F.Hoffmann-La Roche Ag | Heterocyclic gamma secretase modulators |
| WO2010077582A1 (en) | 2008-12-16 | 2010-07-08 | Merck Sharp & Dohme Corp. | Triazole derivatives for treatment of alzheimer's disease |
| US8575150B2 (en) | 2008-12-16 | 2013-11-05 | Merck Sharp & Dohme Corp. | Triazole derivatives for treatment of Alzheimer's disease |
| PA8854101A1 (es) | 2008-12-18 | 2010-07-27 | Ortho Mcneil Janssen Pharm | Derivados de imidazol bicíclicos sustituidos como moduladores de gamma secretasa |
| JP2012513399A (ja) | 2008-12-22 | 2012-06-14 | シェーリング コーポレイション | γ−セクレターゼ調節剤 |
| CA2747750A1 (en) | 2008-12-22 | 2010-07-01 | Theodros Asberom | Gamma secretase modulators |
| TW201030002A (en) | 2009-01-16 | 2010-08-16 | Bristol Myers Squibb Co | Bicyclic compounds for the reduction of beta-amyloid production |
| MX2011008335A (es) | 2009-02-06 | 2011-09-06 | Ortho Mcneil Janssen Pharm | Novedosos compuestos heterociclicos biciclicos sustituidos como moduladores de la gamma secretasa. |
| TWI461425B (zh) * | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| JP2012051805A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | テトラヒドロトリアゾロピリジン誘導体の製造方法 |
| JP2012051806A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | イミダゾリルピラジン誘導体 |
| JP2012121809A (ja) | 2009-02-26 | 2012-06-28 | Eisai R & D Management Co Ltd | 多環式化合物の製造法およびその中間体 |
| JP2012051807A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | アリールイミダゾール化合物 |
| AU2010218667A1 (en) | 2009-02-26 | 2011-07-21 | Eisai R&D Management Co., Ltd. | Salt of tetrahydrotriazolopyridine derivative and crystal thereof |
| WO2010100606A1 (en) | 2009-03-03 | 2010-09-10 | Pfizer Inc. | Novel phenyl imidazoles and phenyl triazoles as gamma-secretase modulators |
| JP6106745B2 (ja) | 2012-05-16 | 2017-04-05 | ヤンセン ファーマシューティカルズ，インコーポレーテッド | （特に）アルツハイマー病の治療に有用な置換３，４−ジヒドロ−２Ｈ−ピリド［１，２−ａ］ピラジン−１，６−ジオン誘導体 |
| WO2015140614A1 (en) | 2014-03-21 | 2015-09-24 | Align Technology, Inc. | Segmented orthodontic appliance with elastics |
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